From bread runs to boardrooms: Megan Oglesby on community, career paths, and investing in the MLS game

In a recent When I Grow Up conversation, Megan Oglesby, Principal Investor for Carolina Core FC, shared her insights on a range of topics, from the pivotal moments that shaped her career to her vision for the new soccer club and her approach to investing. Her journey, marked by a deep commitment to community and a practical understanding of career development, offers valuable lessons for students and professionals in the game.

Megan, you have a clear passion for this. What was the core reason you said "yes" to sharing your story with us today?

Megan Oglesby: I said "yes" because I truly appreciate your efforts to expose young people to both the opportunities and the challenges of pursuing their desired careers. I believe in the power of storytelling – hearing honest experiences, especially the hard-earned lessons. If we could go back and advise our younger selves in college, what would we say? Your platform provides that kind of insight, hopefully helping students navigate their paths with a bit more speed and less difficulty.

Thinking back to those hard-earned experiences, what's a key takeaway you'd share with your younger self?

Megan Oglesby: Advocate for yourself. It took me a while – probably through a few different jobs – to realize the importance of clearly communicating my career aspirations and even my dislikes to my direct boss. Don't assume others know what you want or don't want. I took on many roles I wasn't particularly good at or passionate about. There's a difference between being passionate about something you're not yet skilled in ("yet" is a powerful word!) and doing something you neither enjoy nor excel at. I wish I had advocated more for roles where I felt I could truly contribute and add value. That's a key message I share with young professionals: pay attention to what you naturally gravitate towards or what you consistently put off – those can be strong indicators of your direction.

How do you still apply that wisdom today?

Megan Oglesby: Especially now, since becoming a principal investor with Carolina Core FC and publicly emphasizing my commitment to people development and access to opportunity. I receive many outreach attempts from entrepreneurs seeking investment. While I'm humbled by these requests, I've learned to be careful not to overextend myself or say "yes" out of obligation to things that don't align with my current goals. It's like on "Shark Tank" – sometimes the sharks decline brilliant ideas because they don't feel they can add value beyond the financial aspect. For me, the potential impact is a significant factor in my investment decisions. My focus right now is very community-centric, and I'm also excited about helping WPSL Pro launch their new league, aiming to contribute my expertise to its development.

Speaking of investing, there's a common myth that you need a lot of money to get started. What's your perspective, especially given your background?

Megan Oglesby: I didn't grow up with significant wealth, so I feel like I bridge two different worlds. A story that's ingrained in who I am is our weekly "bread runs" with my mom. We'd pick up day-old bread from places like Food Lion and Starbucks and deliver it to our local homeless shelter. It was her way of contributing to the community with the resources she had: a car, time, and flexibility. This taught me a powerful lesson: you contribute with what you have. For a long time, that was my time through volunteering. More recently, it's evolved through our family's foundation and opportunities like Carolina Core FC. Soccer, for me, isn't just about the sport. It's a vehicle for job creation and community impact. It's about creating pathways – not just for players, but for staff – to learn and grow, potentially moving on to bigger opportunities. I never envisioned myself as an investor, especially a principal one with a public-facing role. It's required significant personal growth.

What's one core skill or habit that's essential for anyone considering investing in the game, whether it’s career or financially?

Megan Oglesby: Be very curious and very collaborative. Always ask questions and seek a deeper understanding. In my experience, if something seems simple, it rarely is. Also, I never want to be the smartest person in the room. Surround yourself with smart people who have expertise in different areas and who understand your vision. What makes a real difference is having people who are willing to challenge your thinking. I believe in the diversity of thought and being okay with agreeing to disagree. That's a beautiful aspect of humanity.

Can you share an example of how "agreeing to disagree" has led to a positive outcome?

Megan Oglesby: It's often less about the "what" we disagree on and more about the "how" to get there. In the business world, the desired outcome is often shared – success, profitability, etc. – the divergence lies in the approach. Within Carolina Core FC, we've fostered an environment where, once a decision is made after discussion, everyone gets on board, even if they initially disagreed. For example, with merchandise like jerseys, everyone has an opinion. Ultimately, our Chief Marketing Officer makes the final call, and we all support it. She's great at considering different perspectives before deciding the best path forward. We hired her for her expertise, so it makes sense to trust her judgment. As someone wise once said (and I'm paraphrasing!), you hire smart people to tell you what to do.

What final piece of advice would you offer students who might be intrigued by your journey or the possibility of investing one day?

Megan Oglesby: Don't discount smaller organizations, especially early in your career. Often, the smaller the organization, the broader your exposure and responsibilities will be. This can be invaluable for learning and for figuring out your desired path. For instance, if you're interested in sports but unsure of your specific niche, a smaller team can offer experience in various areas. People in smaller organizations are often more willing to teach and expose you to different facets of the business, as long as you're proactive, show a strong work ethic, and express interest. We've had staff members express interest in areas outside their direct roles, like our training facility's construction, simply to learn. This cross-functional understanding can be incredibly beneficial. So, don't overlook the "little guys" – they can offer significant growth opportunities.

That's a fantastic point, and it ties into the importance of self-advocacy you mentioned earlier. It's encouraging to hear how Carolina Core FC fosters that kind of curiosity and growth.

Megan Oglesby: We strive to! It's easier said than done, especially with layers of management. I hope we continue to reinforce the priority of people development at every level. While we have budget constraints like any smaller organization, investing in our people's growth is crucial. Our president and I often aim to be the final interviewers for candidates, focusing less on qualifications (since they've reached that stage) and more on their work style, cultural fit, and goals. I like to ask about their aspirations – are they looking to learn quickly and move on, or do they envision a longer-term local impact? Understanding their goals helps us manage expectations and tailor their experience, even if it means they might eventually move on to a larger organization like an MLS first team. While turnover is challenging, we believe in developing our team, both on and off the field.

Megan, this has been incredibly insightful. Thank you for sharing your journey and valuable advice with us!

Have thoughts on any of this for Megan? DM me. I’d love to share them with her the next time we chat.